CA2252601A1 - Process of preparing 2,2'-(1-methyl-1,2-ethanediylidene)bis¬hydrazine carboximidamide| - Google Patents

Process of preparing 2,2'-(1-methyl-1,2-ethanediylidene)bis¬hydrazine carboximidamide| Download PDF

Info

Publication number: CA2252601A1
Authority: CA; Canada
Prior art keywords: methyl; bis; ethanediylidene; water; hydrazine carboximidamide
Prior art date: 1996-05-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002252601A

Other languages

English (en)

French (fr)

Inventor

Richard Philion

Martin R. Gray

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanofi Aventis France

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-05-30

Filing date

1997-05-19

Publication date

1997-12-04

1997-05-19 Application filed by Individual filed Critical Individual

1997-12-04 Publication of CA2252601A1 publication Critical patent/CA2252601A1/en

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 48
230000008569 process Effects 0.000 title claims abstract description 29
HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 title claims 5
MXWHMTNPTTVWDM-NXOFHUPFSA-N mitoguazone Chemical compound NC(N)=N\N=C(/C)\C=N\N=C(N)N MXWHMTNPTTVWDM-NXOFHUPFSA-N 0.000 claims abstract description 62
239000012535 impurity Substances 0.000 claims abstract description 17
DWJDEJZHYRTMRR-UHFFFAOYSA-N 2,2-dimethoxypropanal Chemical compound COC(C)(OC)C=O DWJDEJZHYRTMRR-UHFFFAOYSA-N 0.000 claims abstract description 14
230000002378 acidificating effect Effects 0.000 claims abstract description 7
OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 claims abstract 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 20
238000003756 stirring Methods 0.000 claims description 15
238000001914 filtration Methods 0.000 claims description 12
206010028980 Neoplasm Diseases 0.000 claims description 11
201000011510 cancer Diseases 0.000 claims description 8
239000007787 solid Substances 0.000 claims description 8
238000001035 drying Methods 0.000 claims description 5
239000002198 insoluble material Substances 0.000 claims description 4
238000001953 recrystallisation Methods 0.000 claims description 4
239000000725 suspension Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
241000124008 Mammalia Species 0.000 claims 2
239000012429 reaction media Substances 0.000 claims 2
230000003381 solubilizing effect Effects 0.000 claims 2
MXWHMTNPTTVWDM-UHFFFAOYSA-N 2-[1-(diaminomethylidenehydrazinylidene)propan-2-ylideneamino]guanidine Chemical compound NC(N)=NN=C(C)C=NN=C(N)N MXWHMTNPTTVWDM-UHFFFAOYSA-N 0.000 claims 1
239000012431 aqueous reaction media Substances 0.000 claims 1
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
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XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 claims 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract description 8
238000002425 crystallisation Methods 0.000 abstract 1
230000008025 crystallization Effects 0.000 abstract 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
238000002360 preparation method Methods 0.000 abstract 1
239000000243 solution Substances 0.000 description 28
238000004128 high performance liquid chromatography Methods 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
229920000768 polyamine Polymers 0.000 description 13
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 12
239000002904 solvent Substances 0.000 description 12
230000000694 effects Effects 0.000 description 11
ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 description 10
238000004809 thin layer chromatography Methods 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 8
238000011084 recovery Methods 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
150000002500 ions Chemical class 0.000 description 7
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210000001519 tissue Anatomy 0.000 description 7
231100000419 toxicity Toxicity 0.000 description 7
230000001988 toxicity Effects 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
241000894007 species Species 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
229940063673 spermidine Drugs 0.000 description 5
230000006820 DNA synthesis Effects 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
125000005638 hydrazono group Chemical group 0.000 description 4
GWUSZQUVEVMBPI-UHFFFAOYSA-N nimetazepam Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 GWUSZQUVEVMBPI-UHFFFAOYSA-N 0.000 description 4
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239000008213 purified water Substances 0.000 description 4
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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239000012491 analyte Substances 0.000 description 3
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OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 3
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QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
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AKRQHOWXVSDJEF-UHFFFAOYSA-N heptane-1-sulfonic acid Chemical compound CCCCCCCS(O)(=O)=O AKRQHOWXVSDJEF-UHFFFAOYSA-N 0.000 description 2
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KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
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QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 1
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BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
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AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
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ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
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150000001241 acetals Chemical class 0.000 description 1
RCWXXVNDIDXOTL-UHFFFAOYSA-N acetic acid;2-oxopropanal Chemical compound CC(O)=O.CC(=O)C=O RCWXXVNDIDXOTL-UHFFFAOYSA-N 0.000 description 1
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238000009835 boiling Methods 0.000 description 1
238000000160 carbon, hydrogen and nitrogen elemental analysis Methods 0.000 description 1
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239000007857 degradation product Substances 0.000 description 1
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150000004683 dihydrates Chemical class 0.000 description 1
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238000005516 engineering process Methods 0.000 description 1
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238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
239000005357 flat glass Substances 0.000 description 1
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125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
231100000414 gastrointestinal toxicity Toxicity 0.000 description 1
210000004392 genitalia Anatomy 0.000 description 1
230000003394 haemopoietic effect Effects 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical group O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
239000012493 hydrazine sulfate Substances 0.000 description 1
229910000377 hydrazine sulfate Inorganic materials 0.000 description 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
238000013332 literature search Methods 0.000 description 1
230000007774 longterm Effects 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
229960003539 mitoguazone Drugs 0.000 description 1
VVTBQCXLZQYGQE-PVTAQEPXSA-N mitoguazone hydrochloride Chemical compound Cl.Cl.NC(N)=N\N=C(/C)\C=N\N=C(N)N VVTBQCXLZQYGQE-PVTAQEPXSA-N 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
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239000003208 petroleum Substances 0.000 description 1
HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
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GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA002252601A 1996-05-30 1997-05-19 Process of preparing 2,2'-(1-methyl-1,2-ethanediylidene)bis¬hydrazine carboximidamide| Abandoned CA2252601A1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US08/655,512 US5659083A (en)	1996-05-30	1996-05-30	Process of preparing 2,2'-(1-methyl-1,2-ethanediylidene) bis[hydrazinecarboximidamide]
US08/655,512		1996-05-30

Publications (1)

Publication Number	Publication Date
CA2252601A1 true CA2252601A1 (en)	1997-12-04

Family

ID=24629193

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002252601A Abandoned CA2252601A1 (en)	1996-05-30	1997-05-19	Process of preparing 2,2'-(1-methyl-1,2-ethanediylidene)bis¬hydrazine carboximidamide\|

Country Status (8)

Country	Link
US (1)	US5659083A (pt)
EP (1)	EP0782984A2 (pt)
JP (1)	JP2000511180A (pt)
AU (1)	AU3068897A (pt)
BR (1)	BR9709766A (pt)
CA (1)	CA2252601A1 (pt)
NO (1)	NO985550L (pt)
WO (1)	WO1997045109A1 (pt)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19739290A1 (de) *	1997-09-08	1999-03-11	Ceos Gmbh	Verfahren zur Beseitigung axialer Bildfehler erster, zweiter und dritter Ordnung bei Korrektur des Öffnungsfehlers dritter Ordnung in elektronen-optischen Systemen
DE10356567A1 (de) *	2003-12-04	2005-07-07	Christian-Albrechts-Universität Zu Kiel	Radiosensibilisatoren und Herstellungsverfahren
CN102924339B (zh) *	2012-11-23	2014-06-04	温州澳珀化工有限公司	一种制备米托胍腙的方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3355491A (en) *	1965-09-09	1967-11-28	Dow Chemical Co	1, 2-ethylenebis
US4520031A (en) *	1981-06-01	1985-05-28	The United States Of America As Represented By The Secretary Of Department Of Health And Human Services	Method for reducing toxic effects of methyl-glyoxal bis-guanylhydrazone

1996
- 1996-05-30 US US08/655,512 patent/US5659083A/en not_active Expired - Fee Related
1997
- 1997-02-18 EP EP97400362A patent/EP0782984A2/en not_active Withdrawn
- 1997-05-19 JP JP09542567A patent/JP2000511180A/ja active Pending
- 1997-05-19 CA CA002252601A patent/CA2252601A1/en not_active Abandoned
- 1997-05-19 WO PCT/US1997/008306 patent/WO1997045109A1/en active Application Filing
- 1997-05-19 BR BR9709766A patent/BR9709766A/pt not_active Application Discontinuation
- 1997-05-19 AU AU30688/97A patent/AU3068897A/en not_active Abandoned
1998
- 1998-11-27 NO NO985550A patent/NO985550L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
BR9709766A (pt)	1999-08-10
AU3068897A (en)	1998-01-05
US5659083A (en)	1997-08-19
NO985550L (no)	1999-01-28
NO985550D0 (no)	1998-11-27
JP2000511180A (ja)	2000-08-29
WO1997045109A1 (en)	1997-12-04
EP0782984A2 (en)	1997-07-09

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RU2073679C1 (ru)	1997-02-20	Производные ксантина или их фармацевтически приемлемые соли, способ получения производных ксантина или их фармацевтически приемлемых солей, фармацевтическая композиция
CA2237650C (en)	2006-10-24	Benzamidoxime prodrugs as antipneumocystic agents
JP2002510320A (ja)	2002-04-02	新規な一酸化窒素放出アミジンおよびエナミン誘導ジアゼニウムジオレート、組成物およびそれらの用途、ならびにその製造方法
Handlon et al.	1988	Thiol reduction of 3′-azidothymidine to 3′-aminothymidine: kinetics and biomedical implications
NZ208417A (en)	1987-07-31	Orally administrable compositions having improved release of antidiabetic substances
US20240024266A1 (en)	2024-01-25	Therapeutic Agent or Prophylactic Agent for COVID-19
JP2002522545A (ja)	2002-07-23	ビピリジンマンガン錯体
JP2000502684A (ja)	2000-03-07	Ｎ―アシルアミノアルキルヒドラジンカルボキシイミダミド類
US4874780A (en)	1989-10-17	Anticancer compounds
IE851260L (en)	1985-11-22	Bis-(4-aminophenyl) sulfone derivatives.
CA2252601A1 (en)	1997-12-04	Process of preparing 2,2'-(1-methyl-1,2-ethanediylidene)bis¬hydrazine carboximidamide\|
Erickson	1955	Reactions of Long Chain Amines. V. Reactions with Sugars1, 2
US4340760A (en)	1982-07-20	Monophenylamine derivatives
GB1578110A (en)	1980-10-29	5 - iodo - 5' - amino - 2',5'-dideoxycytidine and the pharmaceutically acceptable salts thereof
US4372976A (en)	1983-02-08	Novel aryl-aliphatic ketone and its use as an antiviral agent
MXPA98009959A (es)	1999-04-27	Proceso para preparar 2,2'-(1-metil-1,2-etanodiiliden)bis[hidrazincarboximidamida]
EP2540703B1 (en)	2015-05-27	Guanylhydrazone salts, compositions, processes of making and methods of using
US5693673A (en)	1997-12-02	Process of preparing 2,2'-(1-methyl-1,2-ethanediylidene)bis hydrazine caroximidamide!
RU2404191C2 (ru)	2010-11-20	Производные гемина или их фармацевтически приемлемые соли, способ получения, композиция и применение
KR920007236B1 (ko)	1992-08-28	이미노옥타딘 3-알킬벤젠 설포네이트의 제조방법
Parasrampuria	1993	Acetazolamide
NO173822B (no)	1993-11-01	Analogifremgangsmaate for fremstilling av den terapeutisk aktive forbindelse (4-amino-2,6-dimetylfenylsulfonyl)nitrometan og farmasoeytisk akseptable salter derav
JP3954096B2 (ja)	2007-08-08	レトロウイルス感染を阻害するための医薬組成物
US3621056A (en)	1971-11-16	Substituted benzylideneamino guanidines

Legal Events

Date	Code	Title	Description
2002-05-21	FZDE	Discontinued